What is the most interesting question you can ask to get to know someone?
12.06.2025 00:00
80~ Share your top three fantasies/desires. (Be detailed) đ
82~ Do you have any fantasies involving Role-Playing?
Doctor/Nurse Stripper/Client
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43~ Ever had your hair pulled during sex? Did you like it? Would you like me to do it?
20- Whatâs your favorite candy? Whatâs your least favorite?
7-What do I do in bed that drives you wild? How about, what turns you off?
13~ Is there a difference between, making love, having sex, and fucking?
34- Ever been to a concert? What was your favorite? Who would you like to see?
20~ Have you ever cheated? Care to Share? If you have, why do you believe that you did?
26- Do you cry while watching a movie or TV show? Which one did you cry the hardest?
What have you learned about yourself that you did not before this?
44~ Care to share something about yourself that no one else knows about you?
54~ Would you ever go skinny dipping with your partner? Have you ever been? Care to Share?
What was the longest? What was the shortest?
These go from easy to answer, to OMG, you really want to know that?! to some serious thought. Take your time and have fun with this. The past is the past⌠it got you two here togetherâŚ
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Foot fetishes, Role-playing, Sadism, Masochism, Bondage, Discipline, Dominance and submission, Voyeurism, Exhibitionism, Furries, Humiliation, Gender/Age play, Cuckolding, Gagging, etc.?
7- Whatâs your favorite book? Do you have a favorite genre? Do you a least favorite?
I would allow you to do it⌠What would you do to me?
*** Questions about Relationships/Past ***
13- How about having a certain hair cut/style?
48~ Have you ever paid or been paid for sex?
How does Bollywood influence Indian culture?
10~ How many dates are necessary before you to have sex with someone?
30- Do you prefer living in the countryside, in a town, or in a big city? Why?
Would/have you gotten a lap dance? Would/have you watched your partner get a lap dance?
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10- What is your favorite family tradition? Whatâs your least favorite?
47~ Have you ever thought about trying tantric sex? (Not sure? Look it up)
85~ If I gave you a âFree Passâ for you to do anything to me for one hour, knowing that no matter what you did,
What is the hidden meaning behind 'Skibidi Ohio', and why is it trending?
33- If you could visit any time period, when would you pick? Please explain why?
46~ Where do you want to be in your life in a year? How about 5 years? How about 10 years?
Prisoner/Prison Guard Landlord/Tenant
74~ Have you ever had sex while others watched? Have you ever watched others have sex?
5- What do I do outside the bedroom that turns you on? How about, what turns you off?
92~ Everyone needs a âsafeâ word. What is yours?
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47~ What would be your dream job and why?
60~ How important is oral sex? Do you like receiving? Do you like giving?
*** Random Questions ***
Escort/Client Job Applicant/Hiring Manager
55~ Would you ever go to a nude beach/resort with your partner? Have you ever been? Care to Share?
40~ If you could go back in time, and relive your life, with the knowledge you have now, what age would you go back to and why?
24~ What are your expectations in a relationship? (I know a very big question, take your time)
How well do you know me? And some of your thoughts about me
27~ If you could freeze your body but not your mind at a certain age, what age would you be? Explain why.
9- If you could have three wishes, what would they be? Why?
How old are you? Male or Female?
69~ Are you willing to have sex while you or your partner is on their period? How about oral sex?
The Ice Breaker Questions
How many times do you think you have âmade loveâ?
37~ What is the biggest age gap between you and one of your sexual partners? Who? Care to Share?
20- Do you have any tattoos? Are there any you want? Are there any you find sexy/attractive?
Physical Touch - Words of Affirmation - Quality Time - Acts of Service - Receiving Gifts
1~ How old were you when you had your first kiss? Who? Care to Share?
1- What was your first impression of me? Has it changed?
36~ What is your favorite time of day to have sex/make love?
38~ Share your most embarrassing sexual memory?
53~ How much can you tell me about the one thing you are most passionate about?
32~ What are your favorite foreplay activities? Kissing/Touching? Food? Toys? Role Play? Others?
10- Do I have a habit or quirk that you find cute or weird? How about an annoying habit of mine?
28~ What are some things that turn on? What is your biggest turn on?
58~ Have you ever taken Nude or Hard-core photos and/or videos? Care to Share?
If yes, what kind? (Clitoral, Vaginal, G-Spot. Anal, Squirting, A-Spot, Cervix, Breast/Nipple, Touching, non- Touching/Mental)
(Dildo, vibrator, nipple clamp, cock ring, butt plug and tail, couplesâ toys, pocket pussy/sleeves, Ben-wa balls, pumps, gags, strap-on, remote controlled, vibrating panties, ETCâŚ)
3- What Superhero or Superpower would you want to be/have?
6- Is there anything that I do/say that irritates you? How about makes you smile and love to hear it?
Any that are a turn off?
31~ What do you find most attractive sexually and non-sexually in a man/woman? (Body and Personality)
Does the thought excite you? Care to share?
* Which of the following turns you on the most? Do you have any not on this list? Care to share?
2- What do you remember about our first date? Rate it. Rate our first kiss. Rate our first time together.
18- Whatâs your favorite way to relax after a long day? Whatâs your least favorite?
41~ What are you best at in bed? What do you think you are not so good at? Anything you want to get good at?
21- Do you have any piercings? Are there any you want? Are there any you find sexy/attractive?
41~ Are there moments in your past that you would want to change? Please share 3 of them.
65~ Describe the best orgasm youâve ever had? Care to share?
62~ Have you used adult toys?
How many partners have you had oral sex with? Who? Care to Share?
5~ When you first started having sex, was it what you thought it would be?
That one or two things that made you go hmmmm, OMG or wow!
16- Can we talk about your health history? Have you had any surgeries? Any broken bones?
76~ Have you had a threesome? Care to Share?
90~ Have you ever had sex in a Pool or Hot Tub? Would you?
11- Is there something you would like me to do, in any area of our relationship that I have not done, or you want more of?
34~ Do you like the lights on or off during sex?
27- What was/ is nickname? Does it have a meaning behind it?
3~ How old were you when you got to 3rd base? (Touching and stimulating the genitals. Oral sex)
61~ How willing would you be to try new sexual positions?
79~ How important is it to have a partner that will help and encourage you to fulfill your fantasies and desires?
52~ What are your hobbies?
42~ Ever been spanked during sex? Did you like it? Would you like me to do it?
What do you dislike about me? I asked you to be 100% honest.
5- Do you fold or scrunch? (toilet paper while you wipe) 6- How about bad hygiene?
25- Fight, Flight, or Freeze? What is your typical response? Does it change with different settings?
45~ What do you like about yourself? Rate yourself 1-10. (Looks, personality, etc....)
49~ If you could, would you want to be the opposite sex for a day, week, or year?
17- Whatâs your favorite holiday? Whatâs your least favorite?
16~ Do you believe in âsoulmatesâ? Have you found yours? Who? Care to Share?
87~ Do you like it when I used my teeth (lightly)? How do you feel about hickeys?
How long for foreplay? Do you need to have an orgasm? Is afterplay important?
71~ Would you give your partner a hand or foot job? Would you receive one?
Do you like the â69â position? Do you prefer to be on top or bottom?
19- Whatâs your favorite fairytale? Whatâs your least favorite?
28- What are some things that people do that irritate you?
1- Whatâs your favorite animal? Do you a least favorite?
59~ Have/do you masturbate? How often? What do you use? (Toys, Phone sex, Erotica, Hard Core, shower/water, etc) Would you, while your partner watches?
13- Whatâs your favorite drink? Whatâs your least favorite?
7- What are your thoughts on religion? Is there an afterlife?
46~ Have you ever used furniture, or other types of things to aid you while having sex?
3- What was the most surprising thing youâve learned about me throughout our relationship?
25~ How do you feel about PDA? (Public Display of Affection)
Piecing, tattoo, color hair, dress up a certain way, it could be anything⌠Shave meâŚ
26~ What side of the bed do you sleep on?
Would /have you ever given your partner a lap dance and Striptease?
11- How about if they like a certain sports team? 12-How about drinking too much?
35~ Do you like playing music in the background or silence? Is there a sexy song that tends to get you in the mood?
24- What celebrities would you use your hall pass on? How about just dinner, or just hanging out with you?
If you say it, I will stop, and we can talk about it when you are ready.
9- Whatâs your favorite season and why? Whatâs your least favorite?
Would you do it again, and would you rather 2 females or 2 males?
3- Whatâs your favorite smell? Do you a least favorite?
Repairman/Lonely Wife Virgin/Experienced
23~ What do you believe is required to have a successful and healthy relationship? (This is important, take your time, and really think about this)
39~ Share your top three favorite/best memorable sexual experiences. Want to repeat them?
Will you cheat again? How can, you be sure? Define what cheating is to you.
Master/Slave Boss/Maid
91~ Would you ever go into an adult book/toys store with me? Would you buy something?
What is your favorite position? Why?
What is your view on sex? Meaning, When/Where/ How often/
13- What is the craziest/scariest thing you've ever done?
48~ Do you have any siblings? Are you close to your family?
35- Do you like playing board or cards game? What is your favorite? Do you a least favorite?
Can you Deep Throat? Do you like the taste of yourself?
9- How about not brushing their teeth or having bad breath? 10- How about if they cuss too much?
50~ Where would you like to be touched more? Do you have a place that you want to be touched, that no one has, or has only happened a couple times? How about less?
Have you ever? Care to Share?
31- If given a chance to be immortal, would you take it? Why?
64~ When was your very first orgasm? When was your first from having sex? Care to share?
22- What is your favorite childhood memory? What is your least favorite?
8- What's your favorite flavor of ice cream? Do you a least favorite?
Get this wrong and this could mean the end⌠:-) some funny, some notâŚ
Do you have a favorite? Is it ok if your partner does?
Is it ok for a man to perform oral sex after he has ejaculated inside of you?
42~ Whatâs your biggest regret in life?
14 â Is it ok to talk to you while you are on the toilet? 15- Is it ok to eat while on the toilet?
1- Whatâs your (zodiac, astrological) sign? Do you believe this has any meaning in your life?
89~ Do you like taking showers together?
16- Whatâs your favorite vacation you have been on? Whatâs your least favorite? Where would you like to go?
29~ What are some things that turn you off? What is your biggest turn off?
Would you mind if your partner watched it? How about together vs alone?
92~ Have you ever had or have an STD? How many? What was it?
19- Do/have you smoked? What do you prefer? How often?
Would you read them together?
84~ How do you feel about reading/listening to adult stories?
Can you have multiple orgasms? Are you able to have different kinds of orgasms?
Nothing too Serious
If NO, would you ever have one? Would it be with 2 men or 2 women?
*** Questions About Me ***
93~ Now that this really long questionnaire is over, one last question, ok maybe 3âŚ
6- Whatâs your favorite TV series? Do you have a favorite genre? Do you a least favorite?
67~ Do you like it when your partner moans and/or is vocal during sex?
18- How often do you drink alcohol? What is your favorite drink?
68~ Would you ever get your partner up from bed by using oral sex and/or intercourse?
14- Do you have a âDeal Breakerâ, anything that your partner has done or will do, a boundary that once crossed you are done with the relationships?
2- Are you afraid of anything? (Spiders, heights, snakes, etc.) What is your greatest fear?
Are you willing to help and encourage your partner to fulfill their fantasies and desires?
32- What's your greatest talent? Can I see it right now?
5- Have you ever been hypnotized? Would you allow yourself to be?
You know that I will be 100% truthful, so ask.
3- Should Pluto still be considered a planet? 4- How about smoking?
Do you watch it? What is your favorite?
57~ Describe the perfect penis/vagina. Does size really matter? What is too big/small?
50~ How many children do you have? What are their ages?
66~ Whatâs the shortest time itâs ever taken for you to have an orgasm? And the longest?
Do you like it when they show and tell you what they want?
81~ Do you have any kinks and/or fetishes?
Is there a smell that most people do not like that you do? Is there a smell that triggers a memory?
Nurse/Patient Celebrity/Fan
38- If you won the Lottery and got 200 million dollars, what would you do with all that money?
7- What if a person smells a certain way? 8- How about smoking?
12~ Have you ever had a one-nightstand? Was it good, fun, satisfying? Would you do it again?
Would you allow me to shave your legs? How about your pubic hair? How about shower sex?
33~ Share your thoughts on what you believe great sex/love making is to you? How long should it last?
12- Whatâs your favorite food? Whatâs your least favorite?
75~ If your partner wants an orgasm/have sex when you don't desire to have sex, how do you plan to deal with their needs?
37- Do you like your name? If you could change it, what would you change it too?
36- Do you play video games? What is your favorite? Do you a least favorite?
17~ What is the average length of your relationship(s)? What was the longest? Why did they end?
52~ Are you willing to make âthose typesâ of bets with your partner?
11~ Have you ever been caught by your parents or children or others while having sex?
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73~ Have you ever had public sex? Care to share? Have you ever had an orgasm in a public place?
39~ What are your love languages?
70~ Would/do you have/like anal sex?
Any that are a turn off?
If YES, was it with 2 men or 2 women? Did you enjoy it?
If you lose, are you willing to be their sex slave for a day, (anything goes)?
8~ How many times a week would you like to engage in sexual activities? What is the average for you now?
43~ If you could write up to a one-page letter to yourself, what would you say and what age would you send it?
Do you shave/trim your pubic hair? For you guys do you shave your balls?
22~ What is the best pickup line anyone has ever used on you? What was the worst?
51~ What tends to bring a smile to your face?
85~ If you gave me a âfree Passâ to have me do anything for one hour, what would you want me to do to you?
Over time has your thoughts on sex changed?
33- Beach or Mountains? Or is there another place to like better?
Model/Photographer Police/Criminal
Teacher/Student Stranger/One Night Stand
53~ How about wearing no panties or bra at all, while wearing a dress or skirt? How about stockings and Garter Belts?
14- What is an embarrassing moment in your life? How about your most embarrassing?
45~ How do you feel about me blindfolding you? How about blindfolding me?
9~ How many times over your lifetime do you think you have had sex so far?
49~ How many times have you been married? Why did they end?
19~ Who/when was your first âheartbreakâ?
4- What do you like about me? Rate me 1-10. (Looks, personality, overall, etc....)
A comprehensive questionnaire, this should be a fun exercise to get to know each other. Try to give as much detail as possible when answering questions. You can go through this together and talk about each question or fill out the questionnaire as completely as you can and once you are done, go through each question together. If you have been together for a while, it is also fun to try to answer the questions for your partner. Remember this should be fun, so if you do not wish to answer a question you can âPASSâ and not answer. Both should answer honestly and without judgement. (This is important, without judgement) I hope this helps you get closer and strengthens your relationship⌠You can learn a lot about the other person⌠and yourselfâŚ
23- What is your dream job? What was it as a child?
Do you think this brought you closer together?
15~ Have you ever been âin loveâ? Who? Care to Share?
15- What's your favorite saying? What word or phrase is your least favorite?
(Strip poker, truth or dare, spin the bottle, Naked Twister, adult card games Etc.) Have you ever? Care to Share?
14~ When was the first time you said, âI Love Youâ? (romantically) Did you mean it? Who? Care to Share?
18~ Who/when was your first âcrushâ?
7~ How many times in one day have you had sex? Who/When/Where? Care to Share?
22- Do you have any birth marks? How about scars? Care to share how you got them?
83~ How do you feel about Porn?
15- What bad habit do you wish you could quit? Do you have any addictions?
77~ What are your thoughts on swapping or swinging or group sex? Have you ever? Care to Share?
5- Whatâs your favorite movie genre? Whatâs your favorite movie of all time? How many times have you watched it?
Would you ever want to be woken up with oral and/or intercourse?
14- What's your favorite dessert? Do you a least favorite?
What is your favorite toy? Ever wanted to try a specific toy?
If yes, what?
Please share Did you stop?
Will you kiss after your partner has gone down on you? Swallow or spit semen?
If you win, what will you make them do?
78~ Have you ever thought about making out or having sex with someone of the same sex? Care to Share?
44~ Have you ever been tied up during sex? What are your thoughts on bondage?
*** Whatâs Your FavoriteâŚ? ***
17- Have you ever done drugs? Which ones? How often?
What would you say to prove to yourself that it was really you?
Meaning if you ever say it no matter how long we have been together or where we are in the momentâŚ
63~ Is having an orgasm important every time you have sex? Have you ever faked an orgasm?
6~ How many sexual partners have you had? Can you name them all? Can you remember when and where?
* Give a rating for each one (0-100)
*** Deal Breaker Questions ***
11- What's your favorite restaurant? Whatâs your least favorite?
40~ Whatâs the weirdest place youâve ever had sex?
88~ Do you prefer me to be naked or in lingerie, PJâs when you are sleeping?
9- Is there something youâve always wanted to ask me but youâre afraid?
6- Do you have dreams? Can you remember them? What do you usually dream about?
72~ Is it ok to ejaculate on your body, face, ass, breast? How about in your mouth? Is there any place not allowed?
Whatâs the longest time you gone without having sex, after, having it? How much time between the others?
21~ What was the best date you ever went on? What has been the worst?
56~ Would you ever go to a strip club with your partner? Have you ever been? Care to Share?
30~ What's something unexpected that turns you on?
1- Down the back or over the top? (The toilet paper roll) 2- Up or down? (The toilet seat)
29- How superstitious are you?
What have you learned about me that was new and/or surprising?
Would you allow me to clean every part of your body with my soapy hands and fingers?
Do you prefer your partnerâs pubic hair trimmed, Landing Strip, full bush or completely bare?
Family Relation Age Play
4- Whatâs your favorite genre of music? Whatâs your least favorite? Is there a song that triggers a memory?
8- What's something unexpected that turns you on that I do to you? Donât be shy now, I really want to know.
2~ How old were you when you got to 2nd base? (Tongue kissing, breast feeling, or outside the clothes genital contact) Who? Care to Share?
4- For a pet, Cat, dog or other?
12- What is the weirdest thing you've ever eaten?
2- Whatâs your favorite color? Do you a least favorite?
4~ How old were you when you lost your virginity? Is it a good memory? Who? Care to Share? (be detailed)
21- What's your favorite way to spend a weekend or time off?
How do you feel about anal play? (Fingers, toys, butt plug) How do you feel about rimming? (licking)
How about if they talk dirty and/or call you names?
8- What are your thoughts on politics?
10- List 5 of your top pet peeves.
51~ Are you willing to play adult games with your partner?
11- List at least 5 things on your bucket list. Have you done any of them already?